I’m doing the free trial and 2 of my 4 rides have not automatically uploaded to Strava. I already know about the file download “work around”. When I upload the file manually it doesn’t sync up with my Strava as well. A “work around” is not a good solution. I want to sign up for a paid account but I’m not going to until this gets sorted out.

You’ll typically see this happening if you get a high number of delay/latency or disconnection from the Internet while saving a ride. While riding It’s hard to see any network fluctuation as your game will allow you to continue to ride.